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Synthetic method for 2, 2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt

A technology of benzothiazole and synthesis method, which is applied in the field of synthesis of 2,2'-azino-didiammonium salt, can solve the problems that it is not suitable for industrial production of ABTS, does not conform to environmental friendliness and green chemical atom economy, etc. Achieve the effect of simple operation, high purity and high yield

Inactive Publication Date: 2013-05-01
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, unfriendly reagents such as strong oxidant sodium nitrite and reducing agent lithium aluminum tetrahydrogen are used in this method, and oxo-3-ethyl-2-iminobenzothiazole hydrazone is a strong carcinogenic compound, which is not environmentally friendly. and Atom Economy Standards for Green Chemistry
Therefore this route is not yet suitable as a method for industrialized production of ABTS

Method used

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  • Synthetic method for 2, 2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt
  • Synthetic method for 2, 2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt
  • Synthetic method for 2, 2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] step one:

[0040] Mix 48.47g of N-ethylaniline with 60ml of H 2 O was added to a 500ml three-necked flask, stirred at room temperature for 5 minutes, then 40ml of concentrated hydrochloric acid was added to the mixture, and 116.62g of KSCN was added, stirred for 10min, then heated to 95°C for reflux reaction for 18h. As the temperature increased, the system The color turns from red to orange and finally to yellow. Cool the reflux system in an ice bath, filter with suction, and 2 O wash, followed by one wash with ethanol. The obtained yellow crude product was recrystallized from ethanol, and then suction filtered to obtain 61.66 g of white powdery solid, with a yield of 94%.

[0041] Step two:

[0042] Put 100 grams of N-ethyl-N-phenylthiourea in a 500ml three-necked flask with 75mlCHCl 3 Dissolve, then add 29ml of elemental bromine in CHCl dropwise with a constant pressure dropping funnel 3 (30ml) mixed solution, control the temperature at 0-20°C, after the dropw...

Embodiment 2

[0050] step one:

[0051] Mix 48.47 g (0.4 mol) of N-ethylaniline with 60 ml H 2 O was added to a 500ml three-necked flask, stirred at room temperature for 5 minutes, then 50ml of concentrated hydrochloric acid was added to the mixture, and 87.47 grams (0.8mol) of KSCN was added, stirred for 10min, then heated to 95°C for reflux reaction for 18h. As the temperature increases, the color of the system turns from red to orange, and finally turns to yellow. Cool the reflux system in an ice bath, filter with suction, and 2 O wash, followed by one wash with 95% ethanol. The obtained yellow crude product was recrystallized from ethanol, and then suction-filtered to obtain 53.13 g of a white powdery solid, with a yield of 81%.

[0052] Step two:

[0053] Put 100g of N-ethyl-N-phenylthiourea in a 500ml three-necked flask with 75ml of CHCl 3 Dissolve, then add 35ml CHCl of elemental bromine dropwise with a constant pressure dropping funnel 3 (30ml) mixed solution, control the temp...

Embodiment 3

[0061] step one:

[0062] Mix 48.47 g (0.4 mol) of N-ethylaniline with 60 ml H 2 O was added to a 500ml three-necked flask, stirred at room temperature for 5 minutes, then 40ml of concentrated hydrochloric acid was added to the mixture, and 54.67 grams (0.5mol) of KSCN was added, stirred for 10min, then heated to 95°C for reflux reaction for 18h. As the temperature increases, the color of the system turns from red to orange, and finally turns to yellow. Cool the reflux system in an ice bath, filter with suction, and 2 O wash, followed by one wash with ethanol. The obtained yellow crude product was recrystallized from ethanol, and then suction-filtered to obtain 51.13 g of a white powdery solid, with a yield of 79%.

[0063] Step two:

[0064] Put 100g of N-ethyl-N-phenylthiourea in a 500ml three-necked flask with 75ml of CHCl 3 Dissolve, then add 40ml CHCl of elemental bromine dropwise with a constant pressure dropping funnel 3 (40ml) mixed solution, control the temperat...

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Abstract

The invention provides a synthetic method for 2, 2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt, namely, the synthetic method for ABTS. The method includes the steps as follows: taking N-ethyl aniline as a raw material to react with thiocyanate and generating N-ethyl-N-anilinothiourea; reacting with bromine after separation to prepare N-ethyl-2imidobenzothiazole hydrobromide; then reacting with hydrazine hydrate to prepare the key intermediate 2, 2'-azino-bis (3-ethylbenzothiazoline); using concentrated sulfuric acid for sulfonation; and finally using ammonia water for a neutralization reaction to prepare the target compound ABTS. The method has the advantages of easiness in easy operation, high yield and purity, and the like, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method, in particular to a synthesis method of 2,2'-azino-bis(3-ethyl-benzothiazole-6-sulfonic acid) diammonium salt. technical background [0002] Since Engvall and Perlman (1971) first reported the establishment of enzyme-linked immunosorbent assay (Enzyme-Linked Immunosorbent Assays, ELISA), due to the advantages of fast, sensitive, simple and easy standardization, ELISA has been rapidly developed and widely used. Although the early ELISA hindered its practical application due to insufficient specificity, with the continuous improvement of methods and continuous updating of materials, especially the use of genetic engineering methods to prepare coated antigens, the use of methods targeting a certain antigen surface The specificity of ELISA is greatly improved, and the use of highly computerized ELISA detectors makes ELISA more convenient, practical and standardized, making it the most widely used method. One of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/82
Inventor 陈军民原唐军张祎敏
Owner JIANGXI NORMAL UNIV
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